# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fin110sub

_database_code_depnum_ccdc_archive 'CCDC 1414150'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
1-Ethyl-2-methylimidazolium-hydrosulfide
;
_chemical_name_common            '[EMIm][HS], 1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H11 N2, H1 S1'
_chemical_formula_sum            'C6 H12 N2 S'
_chemical_formula_weight         144.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6023(3)
_cell_length_b                   7.6710(2)
_cell_length_c                   12.7600(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.8620(10)
_cell_angle_gamma                90
_cell_volume                     801.42(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    117
_cell_measurement_theta_min      3.6511
_cell_measurement_theta_max      24.5316

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.323
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            18404
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1993
_reflns_number_gt                1777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR2011 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, C. Giacovazzo, M. Mallamo, A. Mazzone, G. Polidori, 
R. Spagna, J. Appl. Cryst. 2012, 45, 357-361)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (Putz, H. & Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR,
Kreuzherrenstr. 102, 53227 Bonn, Germany.)
;
_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
enCIfer (Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. 
(2004). J. Appl. Cryst. 37, 335-338.)
;
_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.3197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1993
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.51199(14) 0.64933(15) 0.15718(9) 0.0168(2) Uani 1 1 d . . . . .
H2 H 0.4952 0.6820 0.0827 0.020 Uiso 1 1 calc R U . . .
C4 C 0.62188(15) 0.53994(15) 0.32362(10) 0.0186(2) Uani 1 1 d . . . . .
H4 H 0.6958 0.4828 0.3849 0.022 Uiso 1 1 calc R U . . .
C5 C 0.47589(14) 0.61122(15) 0.31927(9) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.4283 0.6143 0.3773 0.022 Uiso 1 1 calc R U . . .
C6 C 0.24879(14) 0.76417(17) 0.17258(10) 0.0203(3) Uani 1 1 d . . . . .
H6A H 0.2612 0.8750 0.1362 0.024 Uiso 1 1 calc R U . . .
H6B H 0.2072 0.7921 0.2349 0.024 Uiso 1 1 calc R U . . .
C7 C 0.12714(16) 0.6494(2) 0.09153(12) 0.0296(3) Uani 1 1 d . . . . .
H7A H 0.1670 0.6237 0.0290 0.044 Uiso 1 1 calc R U . . .
H7B H 0.0219 0.7097 0.0652 0.044 Uiso 1 1 calc R U . . .
H7C H 0.1135 0.5403 0.1277 0.044 Uiso 1 1 calc R U . . .
C8 C 0.77986(15) 0.50910(18) 0.18606(11) 0.0240(3) Uani 1 1 d . . . . .
H8A H 0.8821 0.5317 0.2447 0.036 Uiso 1 1 calc R U . . .
H8B H 0.7800 0.5730 0.1196 0.036 Uiso 1 1 calc R U . . .
H8C H 0.7699 0.3839 0.1701 0.036 Uiso 1 1 calc R U . . .
N1 N 0.40920(12) 0.67848(13) 0.21481(8) 0.0157(2) Uani 1 1 d . . . . .
N3 N 0.64206(12) 0.56671(13) 0.22160(8) 0.0164(2) Uani 1 1 d . . . . .
S1 S 0.12239(4) 0.70021(4) 0.42922(2) 0.02247(12) Uani 1 1 d . . . . .
H1 H 0.045(4) 0.581(4) 0.444(2) 0.104(10) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N3 1.3285(15) . ?
C2 N1 1.3310(14) . ?
C2 H2 0.9500 . ?
C4 C5 1.3551(17) . ?
C4 N3 1.3804(15) . ?
C4 H4 0.9500 . ?
C5 N1 1.3795(15) . ?
C5 H5 0.9500 . ?
C6 N1 1.4732(15) . ?
C6 C7 1.5085(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N3 1.4614(15) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
S1 H1 1.18(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C2 N1 108.33(10) . . ?
N3 C2 H2 125.8 . . ?
N1 C2 H2 125.8 . . ?
C5 C4 N3 106.52(10) . . ?
C5 C4 H4 126.7 . . ?
N3 C4 H4 126.7 . . ?
C4 C5 N1 107.22(10) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
N1 C6 C7 111.43(10) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 N1 C5 108.73(10) . . ?
C2 N1 C6 125.41(10) . . ?
C5 N1 C6 125.84(10) . . ?
C2 N3 C4 109.19(10) . . ?
C2 N3 C8 124.17(10) . . ?
C4 N3 C8 126.60(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C4 C5 N1 0.54(13) . . . . ?
N3 C2 N1 C5 -0.33(13) . . . . ?
N3 C2 N1 C6 -178.77(10) . . . . ?
C4 C5 N1 C2 -0.15(13) . . . . ?
C4 C5 N1 C6 178.29(11) . . . . ?
C7 C6 N1 C2 70.78(15) . . . . ?
C7 C6 N1 C5 -107.40(13) . . . . ?
N1 C2 N3 C4 0.68(13) . . . . ?
N1 C2 N3 C8 178.52(11) . . . . ?
C5 C4 N3 C2 -0.76(13) . . . . ?
C5 C4 N3 C8 -178.54(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 S1 0.95 2.98 3.7814(12) 143.1 .
C4 H4 S1 0.95 2.79 3.7314(12) 172.7 3_666
C2 H2 S1 0.95 2.68 3.5199(12) 148.2 4_675
C6 H6B S1 0.99 2.88 3.7857(13) 152.7 .
C8 H8A S1 0.98 2.92 3.8535(14) 160.6 1_655

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method Sublimation
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic, Oxygen-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FIN1072


_database_code_depnum_ccdc_archive 'CCDC 1414154'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
; 
N-butyl-N-methylpyrrolidinium hydrosulfide
;
_chemical_name_common            '[BMPyr][HS] (5)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H20 N, H S'
_chemical_formula_sum            'C9 H21 N S'
_chemical_formula_weight         175.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           135
_space_group_name_H-M_alt        'P 42/m b c'
_space_group_name_Hall           '-P 4c 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z-1/2'
'-y, x, -z-1/2'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-y-1/2, -x-1/2, z-1/2'
'y-1/2, x-1/2, z-1/2'

_cell_length_a                   15.6635(6)
_cell_length_b                   15.6635(6)
_cell_length_c                   8.9408(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2193.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3911
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.43

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   
;
Bruker: SADABS v2012/1, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16725
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1154
_reflns_number_gt                871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, 
R. Spagna, J. Appl. Cryst. 1999, 32, 115-119)
;
_computing_structure_refinement  
;
SHELXL-2014/6 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (Putz, H. & Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR,
Kreuzherrenstr. 102, 53227 Bonn, Germany.)
;
_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
enCIfer (Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. 
(2004). J. Appl. Cryst. 37, 335-338.)
;
_refine_special_details          
; 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+2.1128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1154
_refine_ls_number_parameters     90
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1535
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.325
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1773(4) 0.0838(3) -0.1366(5) 0.0428(12) Uani 0.5 1 d D . P . .
H1A H 0.1443 0.1142 -0.2146 0.051 Uiso 0.5 1 calc R U P . .
H1B H 0.1669 0.0217 -0.1459 0.051 Uiso 0.5 1 calc R U P . .
C2 C 0.2694(4) 0.1037(4) -0.1475(6) 0.0439(13) Uani 0.5 1 d . . P . .
H2A H 0.2973 0.0641 -0.2185 0.053 Uiso 0.5 1 calc R U P . .
H2B H 0.2773 0.1627 -0.1849 0.053 Uiso 0.5 1 calc R U P . .
C3 C 0.3081(2) 0.0952(2) 0.0000 0.0439(9) Uani 1 2 d S T P . .
H3A H 0.3384 0.1482 0.0286 0.053 Uiso 0.5 1 calc R U P . .
H3B H 0.3489 0.0470 0.0022 0.053 Uiso 0.5 1 calc R U P . .
C4 C 0.2311(4) 0.0781(3) 0.1072(5) 0.0340(11) Uani 0.5 1 d D . P . .
H4A H 0.2351 0.1117 0.2008 0.041 Uiso 0.5 1 calc R U P . .
H4B H 0.2246 0.0168 0.1312 0.041 Uiso 0.5 1 calc R U P . .
C5 C 0.1534(3) 0.2085(3) -0.0454(5) 0.0384(14) Uani 0.5 1 d . . P . .
H5A H 0.2107 0.2345 -0.0358 0.046 Uiso 0.5 1 calc R U P . .
H5B H 0.1346 0.2140 -0.1507 0.046 Uiso 0.5 1 calc R U P . .
C6 C 0.0914(3) 0.2532(3) 0.0561(6) 0.0442(12) Uani 0.5 1 d . . P . .
H6A H 0.1136 0.2536 0.1598 0.053 Uiso 0.5 1 calc R U P . .
H6B H 0.0359 0.2230 0.0556 0.053 Uiso 0.5 1 calc R U P . .
C7 C 0.0797(3) 0.3453(2) 0.0000 0.0588(11) Uani 1 2 d S T P . .
H7A H 0.1351 0.3748 -0.0133 0.071 Uiso 0.5 1 calc R U P . .
H7B H 0.0469 0.3475 -0.0946 0.071 Uiso 0.5 1 calc R U P . .
C8 C 0.0295(5) 0.3815(6) 0.1299(12) 0.106(3) Uani 0.5 1 d . . P . .
H8A H 0.0188 0.4423 0.1127 0.159 Uiso 0.5 1 calc R U P . .
H8B H 0.0623 0.3743 0.2224 0.159 Uiso 0.5 1 calc R U P . .
H8C H -0.0250 0.3512 0.1386 0.159 Uiso 0.5 1 calc R U P . .
C9 C 0.0767(3) 0.0725(3) 0.0847(6) 0.0447(12) Uani 0.5 1 d . . P . .
H9A H 0.0241 0.0916 0.0358 0.067 Uiso 0.5 1 calc R U P . .
H9B H 0.0768 0.0916 0.1891 0.067 Uiso 0.5 1 calc R U P . .
H9C H 0.0798 0.0100 0.0814 0.067 Uiso 0.5 1 calc R U P . .
N1 N 0.15701(19) 0.11190(19) 0.0000 0.0587(11) Uani 1 2 d DS T P . .
S1 S 0.34330(6) 0.34999(6) 0.0000 0.0522(4) Uani 1 2 d S T P . .
H1 H 0.3988 0.3220 0.0000 0.250 Uiso 1 2 d S U P . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.336(5) . ?
C1 C2 1.480(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.457(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.563(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.595(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.502(6) . ?
C5 N1 1.567(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.537(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.513(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.593(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1 C1 1.336(5) 10 ?
N1 C5 1.567(5) 10 ?
N1 C9 1.593(5) 10 ?
N1 C4 1.595(5) 10 ?
S1 H1 0.9737 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 102.9(4) . . ?
N1 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C3 C2 C1 109.0(5) . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 C4 104.5(4) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 N1 97.8(3) . . ?
C3 C4 H4A 112.2 . . ?
N1 C4 H4A 112.2 . . ?
C3 C4 H4B 112.2 . . ?
N1 C4 H4B 112.2 . . ?
H4A C4 H4B 109.8 . . ?
C6 C5 N1 108.5(3) . . ?
C6 C5 H5A 110.0 . . ?
N1 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
N1 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 C7 108.5(4) . . ?
C5 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C8 C7 C6 99.4(5) . . ?
C8 C7 H7A 111.9 . . ?
C6 C7 H7A 111.9 . . ?
C8 C7 H7B 111.9 . . ?
C6 C7 H7B 111.9 . . ?
H7A C7 H7B 109.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 C1 132.1(6) . 10 ?
C1 N1 C5 124.3(3) . 10 ?
C1 N1 C5 95.1(3) 10 10 ?
C1 N1 C5 95.1(3) . . ?
C1 N1 C5 124.3(3) 10 . ?
C1 N1 C9 68.0(3) . 10 ?
C1 N1 C9 119.7(4) 10 10 ?
C5 N1 C9 118.0(3) 10 10 ?
C5 N1 C9 102.8(3) . 10 ?
C1 N1 C9 119.7(4) . . ?
C1 N1 C9 68.0(3) 10 . ?
C5 N1 C9 102.8(3) 10 . ?
C5 N1 C9 118.0(3) . . ?
C9 N1 C9 56.8(4) 10 . ?
C1 N1 C4 105.5(4) . . ?
C5 N1 C4 101.0(3) 10 . ?
C5 N1 C4 120.2(3) . . ?
C9 N1 C4 137.0(3) 10 . ?
C9 N1 C4 99.2(3) . . ?
C1 N1 C4 105.5(4) 10 10 ?
C5 N1 C4 120.2(3) 10 10 ?
C5 N1 C4 101.0(3) . 10 ?
C9 N1 C4 99.2(3) 10 10 ?
C9 N1 C4 137.0(3) . 10 ?
C4 N1 C4 73.9(4) . 10 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 33.2(5) . . . . ?
C1 C2 C3 C4 -6.0(5) . . . . ?
C2 C3 C4 N1 -18.4(4) . . . . ?
N1 C5 C6 C7 -173.4(3) . . . . ?
C5 C6 C7 C8 -170.5(4) . . . . ?
C2 C1 N1 C1 -69.6(7) . . . 10 ?
C2 C1 N1 C5 70.0(6) . . . 10 ?
C2 C1 N1 C5 77.8(4) . . . . ?
C2 C1 N1 C9 179.6(5) . . . 10 ?
C2 C1 N1 C9 -155.8(4) . . . . ?
C2 C1 N1 C4 -45.4(4) . . . . ?
C2 C1 N1 C4 -24.3(4) . . . 10 ?
C6 C5 N1 C1 151.6(4) . . . . ?
C6 C5 N1 C1 -57.3(6) . . . 10 ?
C6 C5 N1 C5 -41.5(3) . . . 10 ?
C6 C5 N1 C9 83.0(4) . . . 10 ?
C6 C5 N1 C9 24.0(4) . . . . ?
C6 C5 N1 C4 -97.2(4) . . . . ?
C6 C5 N1 C4 -174.8(3) . . . 10 ?
C3 C4 N1 C1 40.7(4) . . . . ?
C3 C4 N1 C1 -172.5(7) . . . 10 ?
C3 C4 N1 C5 -89.8(3) . . . 10 ?
C3 C4 N1 C5 -64.9(4) . . . . ?
C3 C4 N1 C9 114.9(4) . . . 10 ?
C3 C4 N1 C9 165.1(3) . . . . ?
C3 C4 N1 C4 28.7(4) . . . 10 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A S1 0.99 2.64 3.470(5) 141.7 15_665
C5 H5A S1 0.99 2.77 3.732(4) 163.3 .
C9 H9C S1 0.98 2.87 3.780(5) 154.0 5_545

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_compound_source        Acetonitrile
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic, Oxygen-sensitive'
